Sales Development Representative, Mid-Market

Hey there! We’re Contact Monkey 👋

Our mission? To power measurable employee engagement worldwide. And we’d love for you to join us!

We provide the best-in-class internal communications software, featuring an easy-to-use, customizable drag-and-drop Email Template Builder. Our solution allows Internal Comms teams to create, send, and track engaging HTML emails directly within Outlook or Gmail, providing crucial 2-way feedback and powerful analytics.

Leading organizations, including global brands like Rogers, IKEA, and Ticketmaster, leverage our powerful tech stack to transform internal communications from ignored to impactful.

We are looking for a high-performing, growth-oriented Sales Development Representative to join our team. This role is pivotal to Contact Monkey’s growth, focusing specifically on Mid-Market accounts (organizations with 1000 to 10,000 employees).

You will work directly with our Director of Sales, playing a foundational role in building and scaling our Mid-Market business development program and driving new pipeline generation. This position requires a strategic mindset to execute targeted Account-Based Marketing (ABM) and sales plays, ensuring we engage the right personas within these complex, high-value organizations to secure meetings and qualify future customers.

Your primary focus is the strategic creation of new sales opportunities within our defined target market.

• Program Development: Support the Sales and Marketing Leadership team to optimize the core outbound ABM MM playbook, personalized email campaigns, scripts and ABM Targeted campaigns.

• Account-Based Marketing (ABM): Execute a targeted, omnichannel ABM approach to optimize conversion rates specifically within Mid-Market accounts.
• Targeted Outreach: Execute sales strategies across multiple channels (Email, Linked In, Phone, Video Messaging) to engage, educate, and establish relationships with new prospective clients and key stakeholders.
• Leveraging Tech Stack: Expertly utilize our technology stack (Salesforce, Sales Navigator, Nooks, Salesloft, Gong, Clay, Zoom Info) to prospect into target accounts, identify key decision-makers, and build a deep pipeline for the sales team.
• Creative Strategy: Actively contribute creative new sales and marketing strategies that help break into complex accounts and redefine our approach to market challenges.
• Core KPIs: You will be working an estimated 800 Accounts Quarterly across 1625 Target Personas and expected to achieve a minimum 5% conversion.

• Experience: 1+ years of successful, dedicated experience in an outbound sales development capacity.
• Goal Attainment: Proven track record of consistently meeting or exceeding targets (e.g., pipeline or meeting quotas).
• Grit & Drive: Demonstrated relentless persistence and drive to overcome objections, with a natural tendency toward high-quality execution.
• Communication: Strong written and verbal communication skills, characterized by an honest and thoughtful approach that inspires confidence and builds enthusiasm.
• Organizational Mastery: Strong organizational skills and acute attention to detail necessary for building repeatable processes and managing outreach volumes.

• Building repeatable processes and systems that scale across the organization.
• Selling products that make a positive and lasting difference in people's professional lives.
• Seeking the truth behind customer challenges by asking thoughtful, deep questions.
• Going from zero-to-one in uncharted territory to redefine an industry

🏥 100% employer-paid benefits and a health spending account from day one

🌎 Work from anywhere in the world for up to 4 weeks per year

💰 Stock option plan for a stake in our success

🏝 Generous vacation package to take well-deserved breaks

📚 Health and Wellness budget to fuel your growth

🧖 One personal day and two volunteering day to give back to the community

🍎 Five health days per year

💼 Beautiful downtown Toronto office for hybrid work—stocked with…